South Side Vacation Rentals

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Browse Select South Side Vacation Homes

Our top choices for South Side vacation homes

Stylish 4BR South Loop Home State 23-202

10.0 out of 10, Exceptional, (1)
"Very happy with stay. Good communication from property host. "
The price is CA $171
CA $553 total
includes taxes & fees
Sep 2 - Sep 3
Stylish 4BR South Loop Home State 23-202

Relax & Unwind in This Comfortable 3BR Unit

10.0 out of 10, Exceptional, (4)
"Lakeia was very accommodating throughout our stay."
The price is CA $218
CA $463 total
includes taxes & fees
Sep 9 - Sep 10
Relax & Unwind in This Comfortable 3BR Unit

Studio Apt Comfy & Sunlit

The price is CA $127
CA $283 total
includes taxes & fees
Sep 3 - Sep 4
Studio Apt Comfy & Sunlit

Hyde Park Haven | 2BR Retreat

8.0 out of 10, Very good, (1)
"Very neat and nicely decorated, only a couple of issues"
The price is CA $190
CA $393 total
includes taxes & fees
Sep 1 - Sep 2
Hyde Park Haven | 2BR Retreat

Contemporary 2BR Apartment in Vibrant Hyde Park

The price is CA $195
CA $388 total
includes taxes & fees
Sep 16 - Sep 17
Contemporary 2BR Apartment in Vibrant Hyde Park

Furnished 3BR Apt w/ Laundry

10.0 out of 10, Exceptional, (2)
"Apartment and neighborhood were beautiful. We really enjoyed our stay and would book the same place again!"
The price is CA $162
CA $380 total
includes taxes & fees
Sep 2 - Sep 3
Furnished 3BR Apt w/ Laundry

1BR in Prime Hyde Park Apt

The price is CA $138
CA $291 total
includes taxes & fees
Sep 16 - Sep 17
1BR in Prime Hyde Park Apt

Hyde Park 1BR w/ Charm

The price is CA $127
CA $283 total
includes taxes & fees
Sep 3 - Sep 4
Hyde Park 1BR w/ Charm

Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

2.0 star property
10.0 out of 10, Exceptional, (9)
"Very clean in a safe neighborhood. I would stay here again"
The price is CA $197
CA $274 total
includes taxes & fees
Sep 2 - Sep 3
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

Cozy house in the city

2.0 star property
8.8 out of 10, Excellent, (3)
"it was nice"
The price is CA $244
CA $548 total
includes taxes & fees
Sep 1 - Sep 2
Cozy house in the city

Honeycomb Hideout w/ 2 bedrooms

The price is CA $179
CA $580 total
includes taxes & fees
Sep 1 - Sep 2
Honeycomb Hideout w/ 2 bedrooms

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
9.2 out of 10, Wonderful, (10)
"Nice property easy check in. Experience was amazing. Thank you again "
The price is CA $312
CA $629 total
includes taxes & fees
Sep 3 - Sep 4
Spacious 3br home near Chicago, fenced yard for pets

Log Cabin/Funky Jungle at Lakeshore Campground /On Lake/Sleeps 4

10.0 out of 10, Exceptional, (2)
"We liked the location and all of the amenities. "
The price is CA $322
CA $599 total
includes taxes & fees
Sep 8 - Sep 9
Log Cabin/Funky Jungle at Lakeshore Campground /On Lake/Sleeps 4

4BR Retreat w/ Theater, Game Room & Backyard

7.4 out of 10, Good, (9)
The price is CA $80
CA $685 total
includes taxes & fees
Sep 23 - Sep 24
4BR Retreat w/ Theater, Game Room & Backyard

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

9.6 out of 10, Exceptional, (49)
"We had a short stay in this property and we wished it could have been longer. The house was very nice, clean and the communication was great!! It is a short drive to the airport and to downtown. We would definitely stay here again"
The price is CA $209
CA $455 total
includes taxes & fees
Sep 1 - Sep 2
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

2BR, Sleeps7 • Coffee Station, Backyard w/ Grill

The price is CA $93
CA $519 total
includes taxes & fees
Sep 2 - Sep 3
2BR, Sleeps7 • Coffee Station, Backyard w/ Grill

Great Layout – Spacious 2BR Apt

10.0 out of 10, Exceptional, (3)
"Clean, comfortable, and would definitely stay again!"
The price is CA $121
CA $293 total
includes taxes & fees
Sep 22 - Sep 23
Great Layout – Spacious 2BR Apt

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

7.4 out of 10, Good, (8)
"The property was very spacious and clean and customer service is very responsive and quick. "
The price is CA $140
CA $412 total
includes taxes & fees
Sep 2 - Sep 3
Charming 2-bedroom house with WiFi in peaceful Hazel Crest

13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/

2.0 star property
8.4 out of 10, Very good, (5)
"Host was very nice and communicative! Kindly answered all my questions and made our stay amazing. Thanks! "
The price is CA $400
CA $908 total
includes taxes & fees
Sep 2 - Sep 3
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/

Cozy Family Getaway- 4 Blocks From The Beach!

The price is CA $151
CA $405 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Family Getaway- 4 Blocks From The Beach!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top South Side Hotel Reviews

Find out more about South Side

Find out more about South Side

South Side Vacation Homes information

Number of reviews
9
Accommodation
99 Vacation Homes
Lowest Price
Highest Price

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